Diethyl nitromalonate → Methyl 5-phenyl-4-(3,3,3-trifluoropropyl)isoxazole-3-carboxylate

HRID 1804472노트

반응식

HRID 1804472 반응식
[F:1][C:2]([F:14])([F:13])[CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N+:15]([CH:18](C(OCC)=O)[C:19]([O:21][CH2:22]C)=[O:20])([O-])=[O:16].F[P-](F)(F)(F)(F)F.C([N+]1C=CN(C)C=1)CCC>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:7]1([C:6]2[O:16][N:15]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[C:5]=2[CH2:4][CH2:3][C:2]([F:13])([F:14])[F:1])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

참가 물질

6

반응물 3

HCID 97657Diethyl nitromalonateHCID 27341741-Butyl-3-methylimidazolium hexafluorophosphateHCID 58537198Benzene, (5,5,5-trifluoro-1-pentyn-1-yl)-

생성물 1

HCID 67454167Methyl 5-phenyl-4-(3,3,3-trifluoropropyl)isoxazole-3-carboxylate수율 22.1%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of (5,5,5-trifluoropent-1-ynyl)benzene (215 mg, 1.09 mmol), diethyl nitromalonate (0.758 mL, 4.34 mmol), and 1-butyl-3-methylimidazolium hexafluorophosphate (0.023 mL, 0.108 mmol) in toluene (3 mL) was heated to 170° C. for 150 minutes. The reaction mixture was diluted with ethyl acetate (50 mL), washed with water (10 mL), washed with brine (10 mL), and dried over anhydrous sodium sulfate. Concentration followed by purification by silica gel chromatography with hexanes/ethyl acetate (9/1) provided methyl 5-phenyl-4-(3,3,3-trifluoropropyl)isoxazole-3-carboxylate (72 mg). The compound had an HPLC ret. time=3.61 min.−Column. YMC S5 COMBISCREEN® 4.6×50 mm; Gradient time: 4 min; Flow rate=4 ml/min; Solvent A=10% MeOH−90% Water−0.2% H3PO4; Solvent B=90% MeOH−10% water−0.2% H3PO4; Start % B=0; Final % B=100.

후처리

  1. washwashed with water (10 mL)
  2. washwashed with brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationConcentration
  5. customfollowed by purification by silica gel chromatography with hexanes/ethyl acetate (9/1)

출처 및 근거

ORD 기록
ord-7b6e50ec88564368b7715c8330c5648f
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354398B2

반응 노트

불러오는 중…